The only way to know if he or she is your type is to go on that nerve-wracking first date. But, where do you go? The answer is simple: grab a coffee.

Caffeine perks you up. When you meet someone for the first time, your brain starts working in overdrive, processing thousands of signals from about what your date looks like in person, to the outfit they’re wearing, to the way they speak and even how they smell. Give your brain a boost with a stimulating cup of coffee! Caffeine has been proven to banish sleepiness, improve your reaction times, memory and reasoning – all skills that you want to be making the most of on a first date.

To help your conversation go as smooth as possible, we put together a list of 21 questions to ask on your first coffee date!

1. What’s awesome in your life right now?
2. What’s your go-to karaoke song?
3. What did you think you were going to be growing up?
4. What’s the most rebellious thing you did growing up?
5. What’s the strangest compliment you’ve ever gotten?
6. Are you a risk taker or someone who likes to play it safe?
7. If you could only watch one genre of movies for the rest of your life, what would it be?
8. Dog person, cat person, or neither?
9. What’s your guilty pleasure?
10. Do you have any hidden talents or surprising hobbies?
11. What makes you smile without fail?
12. What is your go-to comfort food?
13. What’s the best piece of advice you’ve ever received, and why is it stuck with you?
14. Where would you live if you had no ties to any specific place?
15. What’s the coolest/best/funniest/worst/what have you done thing that’s happened to you lately?
16. What were you like in high school?
17. If you could meet anyone dead or alive, who would it be and why?
18. What made you decide to study [insert college major]?
19. If you could switch careers, without any concern for money, what would you do?
20. What’s your favorite thing to do around here on the weekends?
21. If you could fly anywhere, for free, where would you go?

So, the next time you ask or get asked “Do you want to grab a coffee sometime?” we hope that we’ve equipped you with some questions for great dialogue!